Pyridine → 3,4,5-Trimethoxybenzeneacetyl-1-[(3,4-dimethoxyphenyl)-methylene]isoquinoline

HRID 597242

Reaction equation

HRID 597242 reaction equation
CO[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1OC)[C:9](=[CH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=1)[NH:8][CH2:7][CH2:6]2.N1C=CC=CC=1.C(N(C(C)C)C(C)C)C.[CH3:41][O:42][C:43]1[CH:44]=[C:45]([CH2:53][C:54](Cl)=[O:55])[CH:46]=[C:47]([O:51][CH3:52])[C:48]=1[O:49][CH3:50]>C(Cl)(Cl)Cl.C1C=CC=CC=1>[CH3:52][O:51][C:47]1[CH:46]=[C:45]([CH2:53][C:54]([C:7]2[NH:8][C:9](=[CH:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=3)[C:10]3[C:5]([CH:6]=2)=[CH:4][CH:3]=[CH:12][CH:11]=3)=[O:55])[CH:44]=[C:43]([O:42][CH3:41])[C:48]=1[O:49][CH3:50]

Participants

7

Reactant 4

HCID 1049PyridineHCID 81531DiisopropylethylamineHCID 110321242-(3,4,5-trimethoxyphenyl)acetyl ChlorideHCID 681233913,4-Dihydro-6,7-dimethoxy-1-[(3,4-dimethoxyphenyl)methylene]isoquinoline

Product 1

HCID 867345733,4,5-Trimethoxybenzeneacetyl-1-[(3,4-dimethoxyphenyl)-methylene]isoquinoline

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6212ChloroformSolvent

Procedure

To a suspension of 12 parts of 3,4-dihydro-6,7-dimethoxy-1-[(3,4-dimethoxyphenyl)methylene]isoquinoline in 50 parts of pyridine and 5 parts of N-ethyl-N-(1-methylethyl)-2-propanamine is added a solution of 10 parts of 3,4,5-trimethoxybenzeneacetyl chloride in 45 parts of benzene. The resultant mixture is heated at the boiling point under reflux for 1 hour, then cooled and thereupon diluted with 500 parts of chloroform. The resultant solution is washed with water, dried over anhydrous sodium sulfate, and stripped of solvent by vacuum distillation. The residue is crystallized from a mixture of ethyl acetate and ether to give (Z)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-(3,4,5-trimethoxybenzeneacetyl-1-[(3,4-dimethoxyphenyl)-methylene]isoquinoline melting at 164°-170°.

Workup

  1. temperatureunder reflux for 1 hour
  2. temperaturecooled
  3. washThe resultant solution is washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationstripped of solvent by vacuum distillation
  6. customThe residue is crystallized from a mixture of ethyl acetate and ether

Sources & evidence

ORD record
ord-9277f6817e6345548df65511f3cdca40
Source dataset
uspto-grants-1977_03
Patent number
US04013666

Linked notes

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